Malonic Acid → 3-(5-Bromopyridin-3-yl)prop-2-enoic acid
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.C(O)(=O)[CH2:11][C:12]([OH:14])=[O:13].N1CCCCC1>N1C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:11][C:12]([OH:14])=[O:13])[CH:5]=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 100 °C
Procedure
5-Bromo-pyridin-3-carbaldehyde (15.0 g, 80.6 mmol), malonic acid (18.9 g, 181.4 mmol), and piperidine (6.6 mL, 66.9 mmol) were added to pyridine (48.9 mL). The reaction mixture was stirred at 100° C. for 1 hour, concentrated under reduced pressure, and then distilled water was added thereto. The mixture was filtered and then the resulting solid was dried under reduced pressure to give 28.4 g of the titled compound as a white solid.
Workup
- concentrationconcentrated under reduced pressure
- additiondistilled water was added
- filtrationThe mixture was filtered
- customthe resulting solid was dried under reduced pressure
Sources & evidence
- ORD record
- ord-cef87d08cec1481d9c16f09a397af3e0
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09376420B2
Reaction notes
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